HCID 15550692, compound → HCID 17892901, compound

HRID 489479Notes

Reaction equation

HRID 489479 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[Na].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1([C:18]([C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=2)=[CH2:19])[CH2:17][O:16]1>CN(C=O)C>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]([OH:16])([C:18]([C:20]1[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=1)=[CH2:19])[CH2:17][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 15550692HCID 15550692, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 17892901HCID 17892901, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium 1,2,4-triazole (12.15 g, 133 mmol) was added to a solution of (2,4-difluorophenyl)-2-[1-(4-iodophenyl)ethenyl]oxirane [34.3 g, 89 mmol, from step (e)] in dry DMF (350 ml) under nitrogen at 70° C. The mixture was stirred for 5 hours, cooled, and the solvent removed under reduced pressure. The residue was partitioned between ether (800 ml) and water (2×500 ml). The organic solution was dried (MgSO4), filtered, and silica gel (60-200μ, 75 g) was added. The ether was removed under reduced pressure and the residual solid was applied to the top of a silica gel column (40-60μ, 300 g) and the product was eluted using hexane and increasing amounts of ethyl acetate (0-75%). The product was obtained as a white foam (23.8 g, 61%), which was characterised by 1H-N.M.R. spectroscopy.

Workup

  1. temperaturecooled
  2. customthe solvent removed under reduced pressure
  3. customThe residue was partitioned between ether (800 ml) and water (2×500 ml)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. additionsilica gel (60-200μ, 75 g) was added
  7. customThe ether was removed under reduced pressure
  8. washthe product was eluted
  9. temperatureincreasing amounts of ethyl acetate (0-75%)

Sources & evidence

ORD record
ord-56b7e61c3423465d8f472f4611a16291
Source dataset
uspto-grants-2005_12
Patent number
US06977302B2

Reaction notes

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